Methanol → (R)-3-carboxy-N,N,N-trimethyl-2-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)propan-1-aminium 2,2,2-trifluoroacetate

HRID 1958733Notes

Reaction equation

[I-].C([O:9][C:10](=[O:37])[CH2:11][C@@H:12]([NH:18][S:19]([C:22]1[S:23][C:24]([C:27]2[N:31]([CH3:32])[N:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[CH:25][CH:26]=1)(=[O:21])=[O:20])[CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15])C1C=CC=CC=1.[OH-:38].[Na+].C[OH:41]>>[F:34][C:33]([F:36])([F:35])[C:29]([O-:41])=[O:38].[C:10]([CH2:11][C@@H:12]([NH:18][S:19]([C:22]1[S:23][C:24]([C:27]2[N:31]([CH3:32])[N:30]=[C:29]([C:33]([F:35])([F:36])[F:34])[CH:28]=2)=[CH:25][CH:26]=1)(=[O:21])=[O:20])[CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15])([OH:37])=[O:9]

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 68743143(R)-4-(benzyloxy)-N,N,N-trimethyl-2-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)-4-oxobutan-1-aminium iodide

Product 1

HCID 86641226(R)-3-carboxy-N,N,N-trimethyl-2-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)propan-1-aminium 2,2,2-trifluoroacetateYield 44%

Procedure

To a solution of (R)-4-(benzyloxy)-N,N,N-trimethyl-2-(5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophene-2-sulfonamido)-4-oxobutan-1-aminium iodide in MeOH (1 mL) was added 1 N NaOH (1 mL). The reaction was stirred for 1 h and acidified to pH 1. The mixture was purified by preparatory HPLC to give the title compound as a white solid (12 mg, 44%). 1H NMR (400 MHz, CD3OD) δ 7.67 (d, 1H, J=3.8 Hz), 7.31 (d, 1H, J=3.9 Hz), 6.83 (s, 1H), 4.29-4.26 (m, 1H), 3.87 (s, 3H), 3.62-3.56 (m, 1H), 3.42-3.39 (m, 1H), 3.16 (s, 9H), 2.47-2.41 (m, 1H), 2.19-2.15 (m, 1H); MS ESI 455.2 [M+H]+, calcd for [C16H21F3N4O4S2+H]+ 455.10

Workup

customThe mixture was purified by preparatory HPLC

Sources & evidence

ORD record: ord-3b9c133703f64d52a3a865c2d50bb879
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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